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Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione

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Abstract

—The reaction of 2-amino-1,4-naphthoquinones with ninhydrin at 50–60°C in acetic acid leads to 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones. The products were isolated as hydrates, and, when heated in DMSO with methanesulfonic acid or in acetic acid in the presence of sulfuric acid, they converted into 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones. The rate of the conversion of 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones to 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones in solutions of sulfuric acid in acetic acid is linearly related to the Hammett acidity function.

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 18-33-00663).

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Authors and Affiliations

  1. Astaf’ev Krasnoyarsk State Pedagogical University, ul. A. Lebedevoi 89, Krasnoyarsk, 660049, Russia

    L. M. Gornostaev, O. I. Fominykh, T. I. Lavrikova & Yu. G. Khalyavina

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrentieva 9, Novosibirsk, 630090, Russia

    Yu. V. Gatilov

  3. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    Yu. V. Gatilov

  4. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    G. A. Stashina

Authors
  1. L. M. Gornostaev
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  2. O. I. Fominykh
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  3. T. I. Lavrikova
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  4. Yu. G. Khalyavina
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  5. Yu. V. Gatilov
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  6. G. A. Stashina
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Corresponding authors

Correspondence to L. M. Gornostaev or G. A. Stashina.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1751–1761.

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Gornostaev, L.M., Fominykh, O.I., Lavrikova, T.I. et al. Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione. Russ J Org Chem 55, 1716–1725 (2019). https://doi.org/10.1134/S1070428019110125

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